Words: Ashley Gruber. Photos: Ashley and Jered Gruber.If you ever get the chance to chase one of the Spring’s Monuments – whether it be Italy’s Milano-Sanremo, Flanders’s Ronde van Vlaanderen, France’s, scratch that, Flanders’s Paris-Roubaix, or Wallonia’s Liege-Bastogne-Liege – do yourself a favor: find a person who lives for that race, a person that looks forward to the next edition of the race the minute it ends each year. The opportunity to be taken behind the scenes and shown the race from the eyes of someone who dreams about that particular race will change how you look at that race forever.

Alessandro Federico is that man for Milano-Sanremo. He comes every year, and he does it because he loves it plain and simple. We met Ale for the first time ever at the start in Milano in 2011. It was a great moment to immediately recognize a person we had never met face to face. Just as it’s a great feeling to recognize them, it’s almost disconcerting to shake the hand of a friend for the first time ever, years after making their acquaintance and rapidly becoming friends through the internet and a shared love for cycling.There was no time for niceties though, and with the handshake, the chase began. We’d be in some sort of state of hurry for the next nearly seven hours, as we fought to stay a step ahead of the ever quickening race.

Fast forward five years - another bright morning in Milano - so much has changed, but this morning, everything is exactly as it was before. I get a text telling me what time Ale wants to leave and to meet him by the start line.

Just like five years ago, Ale takes the train in and out of Milan. Parking can be stressful. Why add to the stress? Unlike last time, Ale has my train ticket in his pocket.

The first spot he takes me to is a roundabout. It’s next to a McDonald’s, and it’s objectively an utterly ugly piece of suburban Milano. I was a little surprised to hear Ale say that it was one of his favorites. I couldn’t help but wonder why. There was nothing remarkable about it, at all.

Ale leans over, “This is one of the spots when you really feel the race.”

Sure enough, the race comes raging by - a break is only meters in front of a very active field. When the break goes, the monster will fall back to sleep for some hours, but for now, it’s awake and hungry.

“They are not satisfied with the selection of the break yet. They will continue fighting.”

Sometimes, I forget that I shouldn’t just be looking for a pretty postcard picture. Sometimes, there’s more to it than coastline and snow-capped mountains.

Now we are four. Two other friends and fellow photographers, Angelo and Francesco, have joined Ale on the adventure. He’s the calm and quiet ring leader of this assorted package of fun.

Next: Pontecurone - Ale has been coming to this town for years. The first time we came here, we stopped in a small bakery. Not today.

The announcer goes by - a break of 12 has 8 minutes. Enough time to shoot two spots.

Ale has a trick up his sleeve. He shoots the first spot in a sunny piazza with lots of fans, and after the break passes, he walks down the road and looks up to the balcony. He's been here before. He even sent the signora the photo from last time. She lets him come back to join her small squad on the balcony.

Ale tells me "I was in a good position, I hope I got something good." Angelo has advised him not to look at his photos until the end of the day, lest he get frustrated about missing a shot.

En route to Ovada : “Can we take selfies, Ashley?” Francesco asks, politely. “Because sometimes we do that, and we forgot to ask.”

I laugh. Of course!

The four of us arrive in Ovada, and we learn about the frana. There was a landslide along the coastal road: the Via Aurela. The race will be diverted on to the autostrada for 9km. The problem is that we won't have time once they pass Ovada to get back around them.

Che disastro! The autostrada is closed. Press stickers be damned. We wait. The Italians are in and out of the car a lot talking to the police. Another car is behind us with more photographers. They don't even have the benefit of Stampa stickers - theirs were stolen earlier in the day.

Eventually the police decide to open the gates to the autostrada and escort the traffic to the point of the road closure.

Traffic jam. We calculate that we are less than a kilometer from where they let the riders on - maybe just maaaaaybe we have a chance to see them entering the road, so we sprint down the road, cameras in tow. Ale stays in the car. The responsible adult. We were too late - we could just make out the tiny figures over hundreds of parked cars.

As we walk back, oddly happy and excited, people keep asking what the hell is going on, and why we look so happy.

Che disastro!

Angelo is in the backseat: "Would you like a caramello?"

They speak in English to make me feel comfortable.

We shoot one other spot on the coast - in Spotorno. Ale curses in the heat of the chase, and then apologizes.

Bridge shot in Andora. We have to stay quite close to the car in order to get to our final spot in time - the only spot that really matters - the Poggio.

I mention in the few years since we’ve fledged away from the nest, we learned about a new-old road that would make our lives a much happier place - an easier approach to the all-important final climb of the day.

Ale is game to try something new. I'm a little nervous, as I had only driven it once before, a year ago, and someone had pointed it out to me on the map. I warn Ale that it's a pretty narrow, scary-steep road, but he seems unfazed. Anything better than walking up that God-awful other road - I swear it was 1km at 30%.

A few close encounters, but we made it. We nudge a few cars along at the top and find the last parking spot in the whole town. Ok, not true. Italians can ALWAYS find another parking spot, but that's what it felt like. After the stress of the day, I get a few high fives for the new route (I think that one is a game changer for Ale).

And we all set off to do our own thing. I don't see Ale again that day.

After it was over, I text Ale:

“THANK YOU, Ale!!!! It was so much fun with you guys today. :-) :-)”

The response I get back:

“Yes, we also enjoyed the day!”

I love how casual we can say goodbye. We won’t see Ale for months, but there will be another adventure, another race, and we’ll retrace our steps in a different year - so much the same, so much changing.

For us, it was a day that I’ll never forget. One man’s passion, one man’s lifelong quest to better chase the race of his dreams, gave us a glimpse into a race that deserves its spot amongst the sport’s greatest. It’s a race worthy of its legend.